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Solutions_Manual_for_Organic_Chemistry_6th_Ed 165

Solutions_Manual_for_Organic_Chemistry_6th_Ed 165 - 7-55...

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7 - 55 continued with rearrangement-alkyl shift-ring expansion H �� H 2 C ". .. .-A -�. ("� - H . H C-C-H . . O[ H MAJOR H 2 abstraction of adjacent H gives bridgehead alkene - violates Bredfs Rule 2 I H 2 0 : H H carbocation on 5-membered ring- HOOR A Y! H ('xCH/'RiI .� t - H 2 0 1 ° carbocation-terrible!-will rearrange; can't do hydride shift, must do alkyl shift =
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